| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
The primary application of Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is as a cleavable linker in ADC construction. It does not have a direct biological target itself but enables the targeted delivery of cytotoxic agents to cancer cells. The glucuronic acid-based linker is designed to be cleaved by enzymes such as β-glucuronidase, which are overexpressed in the tumor microenvironment. This allows for selective release of the cytotoxic payload at the tumor site, minimizing off-target toxicity.
|
|---|---|
| ln Vitro |
An ADC cytotoxin is connected to an antibody by use of an ADC linker to form an ADC.
In vitro, Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is used to synthesize ADCs that demonstrate targeted cytotoxicity against cancer cells. The ADC linker is conjugated to an antibody that recognizes a tumor-specific antigen and a cytotoxic payload. In cell-based assays, the resulting ADCs show selective killing of antigen-positive cancer cells while sparing antigen-negative cells. The compound itself is not tested for activity but is evaluated as part of the complete ADC construct. These in vitro studies confirm the functionality and specificity of the ADC linker. |
| ln Vivo |
In vivo, ADCs synthesized using Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 as a linker have demonstrated efficacy in animal models of cancer. The cleavable nature of the linker allows for tumor-selective release of the cytotoxic payload, resulting in tumor growth inhibition with reduced systemic toxicity compared to non-targeted chemotherapy. In vivo studies evaluate tumor growth inhibition, survival benefit, and pharmacokinetic properties of the complete ADC. The linker itself is not administered alone but is an integral component of the therapeutic ADC.
|
| Enzyme Assay |
In vitro enzyme/receptor binding assays for Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 are not typically conducted, as it is a linker intermediate rather than a drug candidate. However, the cleavage efficiency of the glucuronic acid-based linker can be assessed using β-glucuronidase enzyme assays. The linker is incubated with recombinant β-glucuronidase, and the release of the payload is measured by HPLC or mass spectrometry. The aldehyde functionality can be used for conjugation studies with amine-containing molecules. Assays are performed under physiological conditions to mimic the tumor microenvironment.
|
| Cell Assay |
In vitro cell-based assays for Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 are conducted as part of ADC characterization. Complete ADCs synthesized using this linker are tested on cancer cell lines expressing the target antigen. Cells are treated with ADCs at concentrations ranging from 0.01 nM-100 nM for 48-96 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Target specificity is confirmed by comparing cytotoxicity on antigen-positive versus antigen-negative cell lines. Internalization and payload release are evaluated using fluorescently labeled ADCs and confocal microscopy. Experiments include appropriate controls.
|
| Animal Protocol |
In vivo animal studies are conducted with complete ADCs synthesized using Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2, not with the linker alone. Mouse xenograft models are used to evaluate ADC efficacy. ADCs are administered via intravenous injection at doses ranging from 1-30 mg/kg, typically on a weekly or biweekly schedule. Tumor growth is measured by caliper measurements. Pharmacokinetic studies assess ADC stability and payload release. Toxicology studies evaluate off-target toxicity. Each group consists of 6-10 animals with vehicle and unconjugated antibody controls.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 itself are not characterized, as it is an ADC linker intermediate. However, the cleavable glucuronic acid-based linker is designed to improve the pharmacokinetic profile of ADCs by enabling tumor-selective payload release. ADCs incorporating this linker typically have favorable circulation half-lives and reduced systemic exposure of the cytotoxic payload. The linker's cleavage by tumor-associated β-glucuronidase ensures targeted drug delivery. Detailed PK studies are conducted on the complete ADC constructs.
|
| Toxicity/Toxicokinetics |
Toxicological data for Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 are limited, as it is a research intermediate. The compound contains a nitro group, which may require careful handling. The glucuronic acid and acetyl groups are generally considered biocompatible. Comprehensive toxicological profiling has not been conducted for this specific compound. As with all research chemicals, appropriate safety precautions should be taken during handling, including protection from light and moisture. The compound should be used only for in vitro research and ADC synthesis.
|
| References |
[1]. Benatuil, Lorenzo, et al. Anti-B7-H3 antibodies and antibody drug conjugates. WO2017214339.
|
| Additional Infomation |
Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is a cleavable ADC linker used in the development of antibody-drug conjugates for targeted cancer therapy. The glucuronic acid-based linker is designed to be cleaved by β-glucuronidase, an enzyme overexpressed in the tumor microenvironment, enabling selective payload release. The compound features a nitro-substituted phenyl aldehyde for conjugation and triacetylated glucuronic acid for solubility and stability. It is an important building block in ADC research and development. Not approved for clinical use; intended for research purposes only.
|
| Molecular Formula |
C₂₀H₂₁NO₁₃
|
|---|---|
| Molecular Weight |
483.38
|
| Exact Mass |
483.101
|
| CAS # |
148579-93-5
|
| PubChem CID |
10648513
|
| Appearance |
Light yellow to yellow solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
582.6±50.0 °C at 760 mmHg
|
| Flash Point |
219.6±32.1 °C
|
| Vapour Pressure |
0.0±1.6 mmHg at 25°C
|
| Index of Refraction |
1.550
|
| LogP |
2.62
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
13
|
| Rotatable Bond Count |
11
|
| Heavy Atom Count |
34
|
| Complexity |
809
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
O1[C@H]([C@@H]([C@H]([C@@H]([C@H]1C(=O)OC)OC(C)=O)OC(C)=O)OC(C)=O)OC1C=CC(C=O)=CC=1[N+](=O)[O-]
|
| InChi Key |
MHAQOFAFDHVKQE-KVIJGQROSA-N
|
| InChi Code |
InChI=1S/C20H21NO13/c1-9(23)30-15-16(31-10(2)24)18(32-11(3)25)20(34-17(15)19(26)29-4)33-14-6-5-12(8-22)7-13(14)21(27)28/h5-8,15-18,20H,1-4H3/t15-,16-,17-,18+,20+/m0/s1
|
| Chemical Name |
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formyl-2-nitrophenoxy)oxane-2-carboxylate
|
| Synonyms |
MetriacetylβDglucopyranuronatePhaldNO2; Me triacetyl β D glucopyranuronate Ph ald NO2
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~200 mg/mL (~413.75 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.17 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.17 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0688 mL | 10.3438 mL | 20.6877 mL | |
| 5 mM | 0.4138 mL | 2.0688 mL | 4.1375 mL | |
| 10 mM | 0.2069 mL | 1.0344 mL | 2.0688 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
